Simon Stainrod left Falkirk to join Dundee, for an undisclosed fee, on the 31st January 1992. Becoming Dundee’s manager on the 8th May 1992, after a spell as interim manager following the sacking of Iain Munro. He signed a three year contract, and was given a million pound budget from the Chairman, Ron Dixon, to strengthen the squad for the 1992-93 season. Dixon is quoted as saying:
“He has done a superlative job, some would even say magnificent. It’s very difficult to be a player and a coach and be expected to do the job in the office and on the pitch. For that he has the congratulations of the board…”
Jim Duffy was brought back to Dundee as player/coach, basically becoming Strainrod’s assistant manager. The club had to pay Partick Thistle an undisclosed sum to release him from his contract.
The match against Rangers on the 15th August, which Dundee won 4-3, raised Simon’s profile in the media immeasurably. Sporting a trench coat and fedora, he had an air of confidence in the dugout that seemed to embolden the players. In the press conference afterwards he said that the team “hadn’t just gone for Rangers throats, we’d ripped them out.” This of course made headlines in all the newspapers the next day.
Dundee were gaining a reputation for rough play under his stewardship. A 2-2 draw away to Airdrie on the 28th January 1993, saw the Dark Blues end up with nine men on the pitch (This was the second time it had happened that season.) In the previous three matches they had accrued four red cards and seven yellow in their last three matches. This caused Stainrod to speak out in defence of his team:
“When I see we have had seven players sent off this season its unbelievable – we are not dirty, we’re a footballing team who just make a lot of naïve mistakes.”
He was fined £50 by the S.F.A. in April due to his criticism of the referee in the Scottish Cup match against Dumbarton in January. He had been sent off in the first half for a second bookable offence. Dundee went on to win 2-0.
In the boardroom things came to a head in May, when two of Dundee directors tried to oust Stainrod in favour of replacing him with Jim Duffy. After prolonged discussions Ron Dixon publicly backed him. Simon declared that he he would see out the remaining two years of his contract.
It was a turbulent time at the club. Once the boardroom issues were resolved, there were transfer headaches to be resolved. One of which was Andy Dow moving to Chelsea under freedom of contract. Dundee had hoped for a fee of £1 million pounds. After a meeting between the two clubs, Simon along with the clubs directors finally agreed a sum of £2575,000.
Dundee finished tenth in the league that season. They had gone out of the League Cup in the third round, beaten 1-0 by Celtic, and the Scottish Cup in the fourth round losing 2-0 to Hearts.
Stainrod was removed from his post at the by the start of the following season, with Jim Duffy replacing him. He had a new role as Director of Football, and was responsible for the “purchase and sale of playing assets,” and the “administration and recruitment of all the youth policy” as well as running the scouting system throughout Europe.
He finally left Dens Park on the 22nd November 1993, stating that he didn’t want to sit in an office for the rest of his days, he also still harboured ambitions to be “one of the best managers in the business.”